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Synfacts 2011(1): 0018-0018  
DOI: 10.1055/s-0030-1259196
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Substituted Indolizines via a Multicomponent 1,3-Dipolar Cycloaddition Strategy

Contributor(s): Victor Snieckus, Matthew O. Kitching
S. Muthusaravanan, S. Perumal*, P. Yogeeswari, D. Sriram
Madurai Kamaraj University and Birla Institute of Technology and Science - Pilani, Hyderabad, India
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Publication History

Publication Date:
21 December 2010 (online)

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Significance

Reported is the synthesis of indoli­zines via a multicomponent domino reaction sequence starting from pyridines and isoquinolines, bromoacetonitrile or ethyl bromoacetate, and β-nitrostyrenes. The tolerance of the aryl component of the β-nitrostyrenes was investigated, showing little dependence on the aryl substitution pattern. Cyclizations employing isoquinolines and ethyl bromoacetate gave the denitrated products, whereas all other cases gave the nitro-substituted compounds. The activity of these compounds against M. tuberculosis H37RV was investigated with several compounds demonstrating higher ­activity than the standard first line TB drugs ethambutol and ciprofloxacin.